Abstract
Naringin found in citrus fruits is a flavanone glycoside with numerous biological activities. However, the bitterness, low water-solubility, and low bioavailability of naringin are the main issues limiting its use in the pharmaceutical and nutraceutical industries. Herein, a glucansucrase from isolated Leuconostoc citreum NY87 was used for trans-α-glucosylattion of naringin by using sucrose as substrate. Two naringin glucosides (O-α-d-glucosyl-(1′′′′ → 6″) naringin (compound 1) and 4′-O-α-d-glucosyl naringin (compound 2)) were purified and determined their structures by nuclear magnetic resonance. The optimization condition for the synthesis of compound 1 was obtained at 10 mM naringin, 200 mM sucrose, and 337.5 mU/mL at 28 °C for 24 h by response surface methodology method. Compound 1 and compound 2 showed 1896- and 3272 times higher water solubility than naringin. Furthermore, the bitterness via the human bitter taste receptor TAS2R39 displayed that compound 1 was reduced 2.9 times bitterness compared with naringin, while compound 2 did not express bitterness at 1 mM. Both compounds expressed higher neuroprotective effects than naringin on human neuroblastoma SH-SY5Y cells treated with 5 mM scopolamine based on cell viability and cortisol content. Compound 1 reduced acetylcholinesterase activity more than naringin and compound 2. These results indicate that naringin glucosides could be utilized as functional material in the nutraceutical and pharmaceutical industries.
Key points
• A novel O-α-D-glucosyl-(1 → 6) naringin was synthesized using glucansucrase from L. citreum NY87.
• Naringin glucosides improved water-solubility and neuroprotective effects on SH-SY5Y cells.
• Naringin glucosides showed a decrease in bitterness on bitter taste receptor 39.
Graphical Abstract
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Data Availability
All data generated or analyzed during this study are included in this article and its supplementary information files. Further inquiries can be directed to the corresponding author.
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Funding
This study was supported by the Basic Science Research Program through the National Research Foundation of Korea, funded by the Ministry of Education (grant number NRF-2020R1I1A1A01074322) and the Agriculture Science and Technology Development Program (grant number PJ016161) of the Rural Development Administration, the Republic of Korea.
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AI: investigation, formal analysis, writing original-draft; SE: formal analysis, validation. HS: formal analysis, validation, writing; HK: formal analysis, writing—review and editing, validation; JC: formal analysis, and validation; DK: conceptualization, validation, supervision; KY: conceptualization and funding acquisition; SN: conceptualization, supervision, editing, and project administration.
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Ae Eun Im and Sanung Eom contributed equally to this work.
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Im, A.E., Eom, S., Seong, HJ. et al. Enhancement of debitterness, water-solubility, and neuroprotective effects of naringin by transglucosylation. Appl Microbiol Biotechnol 107, 6205–6217 (2023). https://doi.org/10.1007/s00253-023-12709-8
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DOI: https://doi.org/10.1007/s00253-023-12709-8